2-METHOXYESTRONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24O3
Molecular Weight	300.3921
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C(OC)=C4

InChI

InChIKey=WHEUWNKSCXYKBU-QPWUGHHJSA-N

InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H24O3
Molecular Weight	300.3921
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Radioimmunoassay of 2-hydroxyesterone and 2-methoxyestrone in human urine.	1979 May	462497
Metabolism of 2-methoxyestrone in normal men.	1983 Aug	6863476
Altered profile of endogenous steroids in the urine of patients with prolactinoma.	1998 Oct	9812172
Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.	2000 Apr 1	10728588
Inhibition of deoxyglucose uptake in MCF-7 breast cancer cells by 2-methoxyestrone and 2-methoxyestrone-3-O-sulfamate.	2000 Feb 25	10715539
The effects of 2-substituted oestrogen sulphamates on the growth of prostate and ovarian cancer cells.	2003 Feb	12711018
Inhibition of in vitro angiogenesis by 2-methoxy- and 2-ethyl-estrogen sulfamates.	2004 Apr 20	14991574
Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents.	2004 Feb 23	14970876
Selective insensitivity of ZR-75-1 human breast cancer cells to 2-methoxyestradiol: evidence for type II 17beta-hydroxysteroid dehydrogenase as the underlying cause.	2005 Jul 1	15994956
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2005 Jul-Aug	17214292
A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer.	2005 Sep 15	16166441
The role of 17beta-hydroxysteroid dehydrogenases in modulating the activity of 2-methoxyestradiol in breast cancer cells.	2006 Jan 1	16397246
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.	2006 Mar 1	16503607
The Association of the COMT V158M Polymorphism with Endometrial/Ovarian Cancer in HNPCC Families Adhering to the Amsterdam Criteria.	2006 May 15	20223014
2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts.	2006 Oct 1	16619269
Plasma protein binding of the investigational anticancer agent 2-methoxyestradiol.	2006 Sep	16940808
Estrogen metabolism modulates bone density in men.	2007 Apr	17406768
Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells.	2007 Apr 15	17230533
Evaluation of electrospray ionization and atmospheric pressure chemical ionization for simultaneous detection of estrone and its metabolites using high-performance liquid chromatography/tandem mass spectrometry.	2007 Dec 1	17988961
The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers.	2007 Dec 17	18026194
Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.	2007 Feb	17081745
Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer.	2007 Feb	16969706
HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.	2007 Sep	17668912
The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer.	2008 Nov 4	18841154
Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial.	2009 Oct	19577796
Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection.	2010 Apr 15	20188920
The coordinated p53 and estrogen receptor cis-regulation at an FLT1 promoter SNP is specific to genotoxic stress and estrogenic compound.	2010 Apr 21	20422012
Comparison of estrogens and estrogen metabolites in human breast tissue and urine.	2010 Aug 2	20678202
Estrogens and development of pulmonary hypertension: interaction of estradiol metabolism and pulmonary vascular disease.	2010 Dec	20881610
Profiling oestrogens and testosterone in human urine by stable isotope dilution/benchtop gas chromatography-mass spectrometry.	2010 Dec 12	20619283
The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo.	2010 May 21	20492690

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:11:48 GMT 2023` Edited by `admin` on `Fri Dec 15 15:11:48 GMT 2023`
Record UNII	SJ5857RRL3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-METHOXYESTRONE

Common Name

English

ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-2-METHOXY-

Systematic Name

English

2-METHOXY-3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

2-HYDROXYESTRONE 2-METHYL ETHER

Common Name

English

GSS-33

Code

English

2-METHOXY-17-OXOESTRA-1,3,5(10)-TRIEN-3-OL

Systematic Name

English

ESTRONE, 2-METHOXY-

Common Name

English

3-HYDROXY-2-METHOXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2181